Structure Database (LMSD)
Common Name
AT-Resolvin D3
Systematic Name
4S,11R,17R- trihydroxy-5Z,7E,9E,13Z,15E,19Z-docosahexaenoic-acid
Synonyms
- AT-RvD3
LM ID
LMFA04030008
Formula
Exact Mass
Calculate m/z
376.224976
Sum Composition
Status
Curated
3D model of AT-Resolvin D3
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
17(R)-Resolvin D3 (17(R)-RvD3) is an aspirin-triggered epimer of resolvin D3 .1 It is produced from docosahexaenoic acid (DHA) by COX-2 in the presence of aspirin via a 17(R)-hydroperoxy DHA (17(R)-HDHA) intermediate and has been found in mouse inflammatory exudates.1,2 17(R)-RvD3 reduces transmigration of isolated human polymorphonuclear cells (PMNs) and induces efferocytosis of apoptotic PMNs by macrophages.2 17(R)-RvD3 (10 ng/animal) reduces transmigration of neutrophils into the peritoneal cavity, as well as decreases the levels of IL-6 and increases the levels of IL-10 in inflammatory exudate in a mouse model of zymosan-induced peritonitis. It activates GPR32 in a β-arrestin reporter assay and increases phagocytosis to a greater degree in CHO cells overexpressing GPR32 compared to mock-transfected cells. 17(R)-RvD3 increases phagocytosis of etoposide-generated tumor cell debris by monocyte-derived macrophages in H460 human lung carcinoma cells in a concentration-dependent manner.3 It also inhibits tumor growth in a mouse model of Lewis lung carcinoma when administered at a dose of 0.6 µg/kg per day.
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
QBTJOLCUKWLTIC-AXRBAIMGSA-N
InChi (Click to copy)
InChI=1S/C22H32O5/c1-2-3-7-12-19(23)14-10-6-11-15-20(24)13-8-4-5-9-16-21(25)17-18-22(26)27/h3-11,13-14,16,19-21,23-25H,2,12,15,17-18H2,1H3,(H,26,27)/b5-4+,7-3-,11-6-,13-8+,14-10+,16-9-/t19-,20+,21-/m1/s1
SMILES (Click to copy)
C(CC[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\C=C\[C@H](O)C/C=C\CC)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
414.63
Topological Polar Surface Area
97.99
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
5
logP
4.32
Molar Refractivity
110.79
Admin
Created at
-
Updated at
2nd Dec 2024